4-((3-fluorobenzyl)amino)benzonitrile | 1021139-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((3-fluorobenzyl)amino)benzonitrile
• 英文别名: 4-(3-Fluorobenzylamino)benzonitrile；4-[(3-fluorophenyl)methylamino]benzonitrile
• CAS: 1021139-14-9
• 化学式: C₁₄H₁₁FN₂
• mdl: MFCD11145716
• 分子量: 226.253
• InChiKey: SGRWHEQOYMOGAG-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  376.4±27.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((3-fluorobenzyl)amino)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-((3'-fluoro)benzylamino)benzylamine
  参考文献：
  名称：

  Merging the Structural Motifs of Functionalized Amino Acids and α-Aminoamides: Compounds with Significant Anticonvulsant Activities

  摘要：

  Functional amino acids (FAAs) and alpha-aminoamides (AAAs) are two classes of antiepileptic drugs (AEDs) that exhibit pronounced anticonvulsant activities. We combined key structural pharmacophores present in FAAs and AAAs to generate a new series of compounds and document that select compounds exhibit activity superior to either the prototypical FAA (lacosamide) or the prototypical AAA (safinamide) in the maximal electroshock (MES) seizure model in rats. A representative compound, (R)-N-4'-((3 ''-fluoro)benzyloxy)benzyl 2-acetamido-3-methoxypropionamide ((R)-10), was tested in the MES (mice, ip), MES (rat, po), psychomotor 6 Hz (32 mA) (mice, ip), and hippocampal kindled (rat, ip) seizure tests providing excellent protection with ED50 values of 13, 14, similar to 10 mg/kg, and 12 mg/kg, respectively. In the rat sciatic nerve ligation model (ip), (R)-10 (12 mg/kg) provided an 11.2-fold attenuation of mechanical allodynia. In the mouse biphasic formalin pain model (ip), (R)-10 (15 mg/kg) reduced pain responses in the acute and the chronic inflammatory phases.

  DOI：

  10.1021/jm100185c
• 作为产物：
  描述：

  3-氟苄胺 、 4-溴苯腈 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以78%的产率得到4-((3-fluorobenzyl)amino)benzonitrile
  参考文献：
  名称：

  Merging the Structural Motifs of Functionalized Amino Acids and α-Aminoamides: Compounds with Significant Anticonvulsant Activities

  摘要：

  Functional amino acids (FAAs) and alpha-aminoamides (AAAs) are two classes of antiepileptic drugs (AEDs) that exhibit pronounced anticonvulsant activities. We combined key structural pharmacophores present in FAAs and AAAs to generate a new series of compounds and document that select compounds exhibit activity superior to either the prototypical FAA (lacosamide) or the prototypical AAA (safinamide) in the maximal electroshock (MES) seizure model in rats. A representative compound, (R)-N-4'-((3 ''-fluoro)benzyloxy)benzyl 2-acetamido-3-methoxypropionamide ((R)-10), was tested in the MES (mice, ip), MES (rat, po), psychomotor 6 Hz (32 mA) (mice, ip), and hippocampal kindled (rat, ip) seizure tests providing excellent protection with ED50 values of 13, 14, similar to 10 mg/kg, and 12 mg/kg, respectively. In the rat sciatic nerve ligation model (ip), (R)-10 (12 mg/kg) provided an 11.2-fold attenuation of mechanical allodynia. In the mouse biphasic formalin pain model (ip), (R)-10 (15 mg/kg) reduced pain responses in the acute and the chronic inflammatory phases.

  DOI：

  10.1021/jm100185c

文献信息

• Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)–H Bonds with Anilines
  作者：Yan-Ling Song、Bei Li、Zhen-Biao Xie、Dan Wang、Hong-Mei Sun

  DOI：10.1021/acs.joc.1c02311

  日期：2021.12.17

  Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of

  基于新型离子 Fe 中咪唑鎓阳离子上 N 取代基的简单变化，实现了苄基 C(sp 3 )-H 键与带有吸电子基团 (EWG) 或供电子基团 (EDG) 的苯胺的铁催化氧化胺化（三）配合物。咪唑鎓阳离子的结构改性导致氧化还原电位和铁金属中心催化性能的调节。使用DTBP作为氧化剂，[HI t Bu][FeBr 4 ]对带有EWG的苯胺表现出最高的催化活性，而[HIPym][FeBr 4 ]对EDG取代的苯胺更有效。这项工作为苄胺提供了替代途径，同时具有广泛的底物范围和铁催化的优点。
• Novel N-Benzylamide Substituted Derivatives of 2-(Acylamido)acetic Acid and 2-(Acylamido)propionic Acids: Potent Neurological Agents
  申请人：Kohn Harold L.

  公开号：US20120232015A1

  公开（公告）日：2012-09-13

  A first aspect of the invention is a compound (sometimes also referred to herein as an “active agent” or “active compound”) of Formula Ia, or more particularly Formula Ib, or a pharmaceutically acceptable salt or prodrug thereof. Compositions thereof and methods of using the same (e.g. for the treatment of a neurological disease) are also described.

  本发明的第一个方面是公式Ia的化合物（有时也在此处称为“活性剂”或“活性化合物”）或更具体地为公式Ib的化合物，或其药物可接受的盐或前药。还描述了其组成物和使用方法（例如，用于治疗神经系统疾病）。
• N-benzylamide substituted derivatives of 2-(acylamido)acetic acid and 2-(acylamido)propionic acids: potent neurological agents
  申请人：Kohn Harold L.

  公开号：US08829033B2

  公开（公告）日：2014-09-09

  A first aspect of the invention is a compound (sometimes also referred to herein as an “active agent” or “active compound”) of Formula Ia, or more particularly Formula Ib, or a pharmaceutically acceptable salt or prodrug thereof. Compositions thereof and methods of using the same (e.g. for the treatment of a neurological disease) are also described.

  本发明的第一个方面是公式Ia或更具体地公式Ib的化合物（有时在本文中也称为“活性物质”或“活性化合物”），或其药学上可接受的盐或前药。还描述了其组成物和使用方法（例如用于治疗神经系统疾病）。
• US20140342989A1
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL N-BENZYLAMIDE SUBSTITUED DERIVATIVES OF 2-(ACYLAMIDO)ACETIC ACID AND 2-(ACY-LAMIDO) PROPIONIC ACIDS: POTENT NEUROLOGICAL AGENTS
  申请人：The University of North Carolina At Chapel Hill

  公开号：EP2509939A2

  公开（公告）日：2012-10-17